Sample Itinerary · Italy
Rome · Pompeii · Sorrento · Capri
What's Included
Not Included
Who This Trip Is For
Couples and culture-first travelers who want Italy's headline sights with room to breathe: private guides in the morning, long lunches after, and a slower second act on the coast. It works beautifully as a honeymoon or anniversary trip, and it's paced for first-time visitors who don't want to feel rushed.
When To Go
April through June and September through October bring warm days, open terraces, and thinner crowds. July and August run hot in Rome and busy on the coast. If you want Capri without the crush, aim for late spring or the first weeks of fall.
Rome
Private airport transfer with a meet and greet assistant who walks you through your Welcome Package. Ease into the city with a self-guided golden hour walk from Janiculum Hill to the Spanish Steps, ending with a nightcap at a rooftop bar with views of the illuminated Vittoriano.
Where to stay
Rome
A private guide leads you through the Colosseum and Roman Forum, revealing the spectacle, politics, and daily rhythms behind the ruins. Evenings are yours with curated dining options including Michelin starred Aroma with its panoramic amphitheater terrace, or rustic Trattoria Da Teo in Trastevere.
Rome
A small group tour (max 8 guests) of the Vatican Museums and Sistine Chapel including the Raphael Rooms, the Gallery of Maps, and Michelangelo's ceiling in the intimate setting it was designed for. The afternoon is yours to explore Rome's 22 Rioni with a curated neighborhood guide.
Rome to Pompeii to Sorrento
High speed train from Rome to Naples (approximately 75 minutes), then a private driver takes you south with a stop at Pompeii where ancient streets, frescoed villas, and gladiator barracks frozen in 79 A.D. await. Continue to Sorrento for dinner at one of the town's beloved local restaurants.
Where to stay
Sorrento
A private two hour walking tour uncovers Sorrento's layers from Greek origins to the dramatic Valley of the Mills gorge and sweeping Bay of Naples views. The afternoon is spent self-guided, tasting limoncello at celebrated producers like I Giardini di Cataldo and Villa Massa.
Capri
Fast jetfoil to Marina Grande for a small group island experience (max 15). A panoramic boat tour circles Capri's rugged coastline and hidden coves before heading up to quiet Anacapri by minibus, then wander the Piazzetta at leisure with boutiques, espresso, and the island's irresistible energy.
Sorrento
A day entirely your own. Unwind by the hotel pool surrounded by citrus trees and ancient walls. Wander Corso Italia for leather goods, ceramics, and hand painted tiles, then end the day with an aperitivo stroll and a spritz at Fauno Bar or a glass at Bollicine.
Sorrento to Naples
Private transfer to Naples for your onward journey. Approximate travel time one hour.
Typical Investment
From $12,000 / couple
Includes hotels, private transfers, and key experiences. International flights not included.
Curated through Journeys with JB's trusted travel partnerships · Fully customizable to your dates, pace and preferences
Questions
Absolutely. This is a starting point, not a fixed package. I'll adjust the pace, hotels, day trips, and length to suit your travel style and dates.
Not at all. Your private guides are all English-speaking, and I'll set you up with local contacts who handle everything from restaurant reservations to transportation logistics.
Fill out the inquiry form below and I'll reach out within 1–2 business days. On our first call we'll talk through your dates, what you're after, and how I work, including any planning fees for a custom itinerary like this one.
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